WO2018050658A1

WO2018050658A1 - Perfuming composition

Info

Publication number: WO2018050658A1
Application number: PCT/EP2017/072933
Authority: WO
Inventors: François-Raphael BALESTRA
Original assignee: Firmenich Sa
Priority date: 2016-09-16
Filing date: 2017-09-12
Publication date: 2018-03-22

Abstract

The present invention concerns a composition comprising a) 4-methyl-2-pentylpyridine; and b) at least one ingredient, in the form of any one of its stereoisomers, selected from the group consisting of at least one ingredient selected from the group consisting of eugenol, phenethylol, cinnamic alcool, benzyl acetate, methyl benzoate, cinnamyl acetate, phenylethyl acetate, phenylacetaldehyde, indol, bornyl acetate, isobornyl acetate linalyl acetate, dihydromyrcenol, eucalyptol, linalol, terpineol, limonene, citral, camphor, menthol and mixture thereof; characterized in that 4-methyl-2-pentylpyridine is present in an amount comprised between 0.02% to 1% w/w, percentage being relative to the total weight of ingredients of lists a) and b); and the use as a perfumery ingredient of said composition.

Description

PERFUMING COMPOSITION

Technical field

The present invention relates to the field of perfumery. More particularly, it concerns a perfuming composition comprising

a) 4-methyl-2-pentylpyridine; and

b) at least one ingredient, in the form of any one of its stereoisomers, selected from the group consisting of eugenol, phenethylol, cinnamic alcool, benzyl acetate, methyl benzoate, cinnamyl acetate, phenylethyl acetate, phenylacetaldehyde, indol, bornyl acetate, isobornyl acetate linalyl acetate, dihydromyrcenol, eucalyptol, linalol, terpineol, limonene, citral, camphor, menthol and mixture thereof;

characterized in that 4-methyl-2-pentylpyridine is present in an amount comprised between 0.02% to 1% w/w, percentage being relative to the total weight of ingredients of lists a) and b).

Following what is mentioned herein, the invention's perfuming composition as a part of a perfuming consumer product and the use of the invention's perfuming composition are also objects of the invention.

Prior art

A multitude of organoleptic notes could be present in a perfume. One of the aspects very appreciated is to have a perfume providing, in addition to its major notes, a freshness and a natural character.

Therefore, there is still a need to provide a composition allowing to boost or to enhance the freshness and especially in compositions conferring spicy, floral, aromatic or citrus note.

The present invention provides a solution to the above mentioned problem by using composition comprising 4-methyl-2-pentylpyridine; and at least one ingredient selected from the group consisting of eugenol, phenethylol, cinnamic alcool, benzyl acetate, methyl benzoate, cinnamyl acetate, phenylethyl acetate, phenylacetaldehyde, indol, bornyl acetate, isobornyl acetate, linalyl acetate, dihydromyrcenol, eucalyptol, linalol, terpineol, limonene, citral, camphor, menthol and mixture thereof; wherein 4- methyl-2-pentylpyridine is present in an specific amount. The addition of 4-methyl-2- pentylpyridine, which has been reported in WO 2011/121469 to impart a green, green bean note, as well as a spicy-bell pepper, paprika note, and a green, pyrazinic bottom note, surprisingly bring to a perfuming composition a freshness and naturality. Said composition has not been disclosed or suggested heretofore. Description of the invention

Surprisingly, it has now been discovered that the addition of 4-methyl-2- pentylpyridine to a perfuming composition imparting a spicy, floral, aromatic or citrus notes allows boosting the freshness, the cooling effect and even the naturality of said composition.

Therefore the first object of the present invention is a perfuming composition comprising

a) 4-methyl-2-pentylpyridine; and

b) at least one ingredient, in the form of any one of its stereoisomers, selected from the group consisting of eugenol, phenethylol, cinnamic alcool, benzyl acetate, methyl benzoate, cinnamyl acetate, phenylethyl acetate, phenylacetaldehyde, indol, bornyl acetate, isobornyl acetate, linalyl acetate, dihydromyrcenol, eucalyptol, linalol, terpineol, limonene, citral, camphor, menthol and mixture thereof;

characterized in that 4-methyl-2-pentylpyridine is present in an amount comprised between 0.02% to 1% w/w, percentage being relative to the total weight of ingredients of lists a) and b);

said composition can be used to impart odor notes of the spicy, floral, aromatic or citrus type having also a freshness aspect.

The ingredient of group b) can be used in the preparation of a variety of perfuming composition imparting various olfactive characters, in particular spicy, floral, aromatic or citrus character. The relative amount of 4-methyl-2-pentylpyridine may vary according to the desired odor. The invention's perfuming composition may comprise 4-methyl-2- pentylpyridine in an amount comprised between 0.02% to 0.4% w/w preferably in an amount comprised between 0.02% to 0.2% w/w; percentage being relative to the total weight of ingredients of lists a) and b); e.g. when the invention's perfuming composition is develop to impart a citrus or aromatic note. The invention's perfuming composition may comprise 4-methyl-2-pentylpyridine in an amount comprised between 0.4% to 1% w/w, percentage being relative to the total weight of ingredients of lists a) and b); e.g. when the invention's perfuming composition is develop to impart a spicy or floral note. According to any one of the above embodiment, at least one ingredient selected from the group consisting of eugenol, phenethylol, cinnamic alcool, benzyl acetate, methyl benzoate, cinnamyl acetate, phenylethyl acetate, phenylacetaldehyde, indol, bornyl acetate, isobornyl acetate, linalyl acetate, dihydromyrcenol, eucalyptol, linalol, terpineol, limonene, citral, camphor, menthol may be in a form of any stereoisomers. Said ingredients of the invention's perfuming composition may be present in natural oil. None limiting examples of such oil includes Pepper oil, artemisia oil, lavender oil, lavandin oil, eucalytus oil, Spanish sage oil, lemon oil, rosemary oil, spearmint oil, bergamot oil, elemi oil, estragon oil, geranium oil, nutmeg oil, neroli oil, petitgrain oil or orange oil. So, the invention's perfuming composition comprising 4-methyl-2-pentylpyridine and natural oil comprising eugenol, phenethylol, cinnamic alcool, benzyl acetate, methyl benzoate, cinnamyl acetate, phenylethyl acetate, phenylacetaldehyde, indol, bornyl acetate, isobornyl acetate, linalyl acetate, dihydromyrcenol, eucalyptol, linalol, terpineol, limonene, citral, camphor or menthol are also part of the present invention.

For the sake of clarity, by the expression "any stereoisomers", or the similar, it is meant the normal meaning understood by a person skilled in the art, i.e. that the compounds can be a pure enantiomer (if chiral) or diastereomer (e.g. the double bond is in a conformation E or Z) or a mixture of enantiomer or diastereoisimer.

The addition of 4-methyl-2-pentylpyridine to a perfuming composition comprising perfuming ingredients imparting spicy, floral aromatic or citrus note despite the organoleptic property of said ingredient which is known to provide a spicy and green note, allows boosting the freshness aspect lacking of the perfuming composition.

According to a particular embodiment, the invention's perfuming composition may be used as a perfume on its own. So, the invention's perfuming composition may consist of 4-methyl-2-pentylpyridine; and at least one ingredient selected from the group consisting of eugenol, phenethylol, cinnamic alcool, benzyl acetate, methyl benzoate, cinnamyl acetate, phenylethyl acetate, phenylacetaldehyde, indol, bornyl acetate, isobornyl acetate, linalyl acetate, dihydromyrcenol, eucalyptol, linalol, terpineol, limonene, citral, camphor, menthol and mixture thereof; characterized in that 4-methyl-2- pentylpyridine is present in an amount comprised between 0.02% to 1% w/w, percentage being relative to the total weight perfuming composition.

A perfuming composition is a complex mixture including a multitude of ingredients imparting different olfactive notes. A perfuming composition is shaped in order to provide an odor presenting different organoleptic facets. So, according to another particular embodiment, the invention's perfuming composition may be part of a more complex perfuming composition wherein the invention composition is added in order to improve the hedonic aspect of a composition, in particular the freshness and / or naturality aspect. So the perfuming composition of the present invention may further comprise optional ingredient such as perfumery carrier, perfuming co-ingredient or perfumery adjuvant. With the addition of optional ingredients, the ingredients of list a) and b) may be present in the composition in an amount comprised between 1% and 99% w/w, percentage being relative to the total weight of ingredients of the composition, preferably between 5% and 90% w/w, even more preferably between 10% and 85% w/w and 4- methyl-2-pentylpyridine may be present in an amount comprised between 0.01 % to 1% w/w, percentage being relative to the total weight of the composition; preferably in an amount comprised between 0.02 % to 0.4% w/w, more preferably in an amount comprised between 0.02 % to 0.1% w/w.

According to a particular embodiment, the invention's perfuming composition may optionally comprise a perfumery carrier. By "perfumery carrier" it is meant here a material which is practically neutral from a perfumery point of view, i.e. that does not significantly alter the organoleptic properties of perfuming ingredients. Said carrier may be a liquid or a solid.

As liquid carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive. However, one can cite as non-limiting examples solvents such as butylene or propylene glycol, glycerol, dipropyleneglycol and its monoether, 1,2,3- propanetriyl triacetate, dimethyl glutarate, dimethyl adipate l,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2- (2- ethoxyethoxy)-l-ethano, tri-ethyl citrate or mixtures thereof, which are the most commonly used. Other suitable perfumery carriers than those previously specified, can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol (origin: Dow Chemical Company), or hydrogenated castors oils such as those known under the trademark Cremophor RH 40 (origin: BASF). Solid carrier is meant to designate a material to which the perfuming composition or some element of the perfuming composition can be chemically or physically bound. In general such solid carriers are employed either to stabilize the composition, or to control the rate of evaporation of the compositions or of some ingredients. The use of solid carrier is of current use in the art and a person skilled in the art knows how to reach the desired effect. However by way of non-limiting example of solid carriers, one may cite absorbing gums or polymers or inorganic material, such as porous polymers, cyclodextrines, wood based materials, organic or inorganic gels, clays, gypsum talc or zeolites.

As other non-limiting examples of solid carriers, one may cite encapsulating materials. Examples of such materials may comprise wall-forming and plasticizing materials, such as mono, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitat, Behr's Verlag GmbH & Co., Hamburg, 1996. The encapsulation is a well-known process to a person skilled in the art, and may be performed, for instance, by using techniques such as spray-drying, agglomeration or yet extrusion; or consists of a coating encapsulation, including coacervation and complex coacervation technique.

As other non-limiting examples of solid carriers, one may cite the core-shell capsules with resins of aminoplast, polyamide, polyester, polyurea or polyurethane type or a mixture thereof (all of said resins are well known to a person skilled in the art) using techniques like phase separation process induced by polymerization, interfacial polymerization, coacervation or altogether (all of said techniques have been described in the prior art), optionally in the presence of a polymeric stabilizer or of a cationic copolymer.

Resins may be produced by the polycondensation of an aldehyde (e.g. formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof) with an amine such as urea, benzoguanamine, glycoluryl, melamine, methylol melamine, methylated methylol melamine, guanazole and the like, as well as mixtures thereof. Alternatively one may use preformed resins alkylolated polyamines such as those commercially available under the trademark Urac^® (origin: Cytec Technology Corp.), Cy mel (origin: Cytec Technology Corp.), Urecoll or Luracoll (origin: BASF).

Other resins are the ones produced by the polycondensation of an a polyol, like glycerol, and a polyisocyanate, like a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate or xylylene diisocyanate or a Biuret of hexamethylene diisocyanate or a trimer of xylylene diisocyanate with trimethylolpropane (known with the tradename of Takenate^®, origin: Mitsui Chemicals), among which a trimer of xylylene diisocyanate with trimethylolpropane and a Biuret of hexamethylene diisocyanate.

Some of the seminal literature related to the encapsulation of perfumes by polycondensation of amino resins, namely melamine based resins with aldehydes includes by articles such as those published by K. Dietrich et al. in Acta Polymerica, 1989, vol. 40, pages 243, 325 and 683, as well as 1990, vol. 41, page 91. Such articles already describe the various parameters affecting the preparation of such core-shell microcapsules following prior art methods that are also further detailed and exemplified in the patent literature. US 4'396'670, to the Wiggins Teape Group Limited, is a pertinent early example of the latter. Since then, many other authors have enriched the literature in this field and it would be impossible to cover all published developments here, but the general knowledge in encapsulation technology is very significant. More recent publications of pertinency, which disclose suitable uses of such microcapsules, are represented for example by the article of H.Y.Lee et al. in Journal of Microencapsulation, 2002, vol. 19, pages 559-569, international patent publication WO 01/41915 or yet the article of S. Bone et al. in Chimia, 2011, vol. 65, pages 177-181.

According to a particular embodiment, the invention's perfuming composition may optionally comprise further at least one perfuming co-ingredient. Said perfuming co- ingredient is not selected from the list consisting of 4-methyl-2-pentylpyridine, eugenol, phenethylol, cinnamic alcool, benzyl acetate, methyl benzoate, cinnamyl acetate, phenylethyl acetate, phenylacetaldehyde, indol, bornyl acetate, isobornyl acetate, linalyl acetate, dihydromyrcenol, eucalyptol, linalol, terpineol, limonene, citral, camphor, menthol. Moreover, by "perfuming co-ingredient" it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect. In other words such a co-ingredient, to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor. The nature and type of the perfuming co-ingredients optionally present in the perfuming composition do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect. In general terms, these perfuming co -ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin.

In particular one may cite perfuming co-ingredients which are commonly used in perfume formulations, such as:

- Aldehydic ingredients: decanal, dodecanal, 2-methyl-undecanal, 10-undecenal, octanal and/or nonenal;

- Aromatic-herbal ingredients: alpha-pinene;

- Balsamic ingredients: coumarine, ethylvanillin and/or vanillin;

- Citrus ingredients: citronellyl nitrile, orange terpenes, l-P-menthen-8-yl acetate and/or 1 ,4(8)-P-menthadiene;

- Floral ingredients: Methyl dihydrojasmonate, Citronellol, phenylethanol, 3-(4-tert- butylphenyl)-2-methylpropanal, hexylcinnamic aldehyde, benzyl salicylate, tetrahydro- 2-isobutyl-4-methyl-4(2H)-pyranol, beta ionone, methyl 2-(methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-l-yl)-3-buten-2-one, hexyl salicylate, 3,7-dimethyl- 1 ,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, verdyl acetate, geraniol, P-menth-l-en-8-ol, 4-(l,l-dimethylethyl)-l-cyclohexyle acetate, 1,1- dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate , high cis methyl dihydrojasmonate, 3-methyl-5-phenyl-l-pentanol, verdyl proprionate, geranyl acetate, tetrahydro linalool, cis-7-P-menthanol, Propyl (S)-2-(l,l- dimethylpropoxy)propanoate, 2-methoxynaphthalene, 2,2,2-trichloro- 1-phenylethyl acetate, 4/3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-l-carbaldehyde, amylcinnamic aldehyde, 4-phenyl-2-butanone, isononyle acetate, 4-(l,l- dimethylethyl)-l-cyclohexyl acetate, verdyl isobutyrate and/or mixture of methylionones isomers;

- Fruity ingredients: gamma undecalactone, 4-decanolide, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma nonalactone, allyl heptanoate, 2- phenoxyethyl isobutyrate, ethyl 2-methyl-l,3-dioxolane-2-acetate and/or diethyl 1,4- cyclohexane dicarboxylate;

- Green ingredients: 2,4-Dimethyl-3-cyclohexene-l-carbaldehyde, 2-tert-butyl-l- cyclohexyl acetate, styrallyl acetate, allyl (2-methylbutoxy)acetate, 4-methyl-3-decen- 5-ol, diphenyl ether, (Z)-3-hexen-l-ol and/or l-(5,5-dimethyl-l-cyclohexen-l-yl)-4- penten-l-one;

- Musk ingredients: l,4-dioxa-5,17-cycloheptadecanedione, pentadecenolide, 3-Methyl- 5-cyclopentadecen-l-one, 1, 3,4,6,7, 8-hexahydro-4,6, 6,7,8, 8-hexamethyl-cyclopenta-g- 2-benzopyrane, (lS, R)-2-[l-(3',3'-dimethyl- -cyclohexyl)ethoxy]-2-methylpropyl propanoate, pentadecanolide and/or (lS, R)-[l-(3',3'-Dimethyl-l'- cyclohexyl)ethoxycarbonyl]methyl propanoate;

- Woody ingredients: l-(octahydro-2,3,8,8-tetramethyl-2-naphtalenyl)-l-ethanone, patchouli oil, terpenes fractions of patchouli oil, ( R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'- cyclopenten-l'-yl)-2-buten-l-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-2- buten-l-ol, Methyl cedryl ketone, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan- 2-ol and/or l-(2,3, 8, 8-tetramethyl- 1,2,3,4,6,7, 8, 8a-octahydronaphthalen-2-yl)ethan-l- one;

- Other ingredients (e.g. amber, powdery spicy or watery): dodecahydro-3a,6,6,9a- tetramethyl-naphtho[2,l-b]furan and any of its stereoisomers, heliotropin, anisic aldehyde, cinnamic aldehyde, clove oil, 3-(l,3-benzodioxol-5-yl)-2-methylpropanal and/or 3-(3-isopropyl- l-phenyl)butanal.

A perfumery co-ingredients according to the invention may not be limited to the above mentioned perfuming co-ingredients, and many other of these co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds.

According to a particular embodiment, the invention's perfuming composition may optionally comprise perfumery adjuvant. By "perfumery adjuvant" we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfuming composition cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art. One may cite as specific non-limiting examples the following: viscosity agents (e.g. surfactants, thickeners, gelling and/or rheology modifiers), stabilizing agents (e.g. preservatives, antioxidant, heat/light and or buffers or chelating agents, such as BHT), coloring agents (e.g. dyes and/or pigments), preservatives (e.g. antibacterial or antimicrobial or antifungi or anti irritant agents), abrasives, skin cooling agents, fixatives, insect repellants, ointments, vitamins and mixtures thereof.

It is understood that a person skilled in the art is perfectly able to design optimal formulations for the desired effect by admixing the above mentioned components of a perfuming composition, simply by applying the standard knowledge of the art as well as by trial and error methodologies.

An invention's composition consisting of at least one invention's composition as defined above and at least one perfumery carrier consists of a particular embodiment of the invention as well as a perfuming composition comprising at least invention's composition as defined above, at least one perfumery carrier, at least one perfumering co- ingredient, and optionally at least one perfumery adjuvant.

For the sake of clarity, it is also understood that any mixture resulting directly from a chemical synthesis, e.g. a reaction medium without an adequate purification, in which the composition of the invention would be involved as a starting, intermediate or end-product could not be considered as a perfuming composition according to the invention as far as said mixture does not provide the inventive composition in a suitable form for perfumery. Thus, unpurified reaction mixtures are generally excluded from the present invention unless otherwise specified.

The invention's composition can also be advantageously used in all the fields of modern perfumery, i.e. fine or functional perfumery, to positively impart or modify the odor of a consumer product into which said composition is added. Consequently, another object of the present invention consists of a perfumed consumer product comprising, as a perfuming ingredient, the invention's composition, as defined above.

The invention's composition can be added as such or as part of an invention's perfuming composition.

For the sake of clarity, "perfumed consumer product" is meant to designate a consumer product which deliver at least a pleasant perfuming effect to the surface or space to which it is applied (e.g. skin, hair, textile, or home surface). In other words, a perfumed consumer product according to the invention is a perfumed consumer product which comprises a functional formulation, as well as optionally additional benefit agents, corresponding to the desired consumer product and an olfactive effective amount of at least one invention's compound. For the sake of clarity, said perfumed consumer product is a non-edible product.

The nature and type of the constituents of the perfumed consumer product do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the nature and the desired effect of said product.

Non-limiting examples of suitable perfumed consumer product include a perfume, such as a fine perfume, a splash or eau de parfum, a cologne or a shave or after- shave lotion; a fabric care product, such as a liquid or solid detergent, a fabric softener, a liquid or solid scent booster, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain-care product; a body-care product, such as a hair care product (e.g. a shampoo, a coloring preparation or a hair spray, a color care product, a hair shaping product, a dental care product), a disinfectant, an intimate care product; a cosmetic preparation (e.g. a skin cream or lotion, a vanishing cream or a deodorant or antiperspirant (e.g. a spray or roll on), a hair remover, a tanning or sun or after sun product, a nail product, a skin cleansing, a makeup); or a skin-care product (e.g. a soap, shower or bath mousse, an oil or a gel, or a hygiene product or a foot/hand care products); an air care product, such as an air freshener or a "ready to use" powdered air freshener which can be used in the home space (rooms, refrigerators, cupboards, shoes or car) and/or in a public space (halls, hotels, malls, etc.); or a home care product, such as a mold remover, a furnisher care, a wipe, a dish detergent or a hard-surface (e.g. a floor, bath, sanitary or a windows) detergent; a leather care product; a car care product, such as a polish, a waxe or a plastic cleaner.

Some of the above-mentioned perfumed consumer products may represent an aggressive medium for the invention's composition, so that it may be necessary to protect the latter from premature decomposition, for example by encapsulation or by chemically binding it to another chemical which is suitable to release the invention's composition upon a suitable external stimulus, such as an enzyme, light, heat or a change of pH.

The proportions in which the composition according to the invention can be incorporated into the various aforementioned products or compositions vary within a wide range of values. These values are dependent on the nature of the article to be perfumed and on the desired organoleptic effect as well as on the nature of the co-ingredients in a given base when the invention's composition according to the invention are mixed with perfuming co-ingredients, solvents or additives commonly used in the art.

When the invention composition are incorporated into perfumed consumer products, other than fine perfumery and air freshener where in general the perfuming composition is the essential constituent of a consumer product, 0.01% to 2% by weight of the invention's composition can be used, percentage being relative to the weight of the article.

Another object of the present invention is the use of a composition as defined above as perfuming ingredient. In other words, it concerns a method or a process to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article or of a surface, which method comprises adding to said composition or article an effective amount of invention's composition as defined above, e.g. to impart its typical note.

According to a particular embodiment, such method is aimed to provide a fresher spicy, floral, aromatic or citrus note. In particular, the addition of 4-methyl-2- pentylpyridine enhances the fresh peppery note in a composition with spicy character, the freshness and the naturality of hyacinth and lilac notes in a composition with floral character, the cooling feeling and the freshness of mint and eucalyptus notes in composition with an aromatic character or the naturality and the cooling effect, bringing a more zesty lime and sorbet aspect of lemon in a composition with a citrus character.

Examples

Example 1

Preparation of a perfuming composition A perfuming composition, of the spicy type, was prepared by admixing the following ingredients: Parts by weight Ingredient

Dipropylene glycol 580

Elemi oil^1} 400

Linalool 800

Muscade oil²⁾ 20

Red berries oil³⁾ 200

2000

1) Comprises around 50 % of ingredients of list b); i.e. limonene and terpineol

2) Comprises around 10 % of ingredients of list b); i.e. limonene, eugenol and terpineol

3) Comprises around 15 % of ingredients of list b); i.e. limonene.

The addition of 2 to 4 parts by weight of 4-methyl-2-pentylpyridine (i.e. 0. 2% to 0.4% of 4-methyl-2-pentylpyridine, percentage being relative to the total weight of ingredients of lists a) and b)) to the above-described composition enhances the fresh peppery note.

The perfuming composition of the spicy type was diluted in dipropylene glycol up to 10000 parts by weight; i.e 7996 to 7998 parts of dipropylene glycol was added respectively to the above-described composition comprising 2 to 4 parts by weight of 4- methyl-2-pentylpyridine.

Example 2 Preparation of a perfuming composition

A perfuming composition, of the citrus type, was prepared by admixing the following ingredients:

Parts by weight Ingredient

Lynalyl acetate 2000

Bergamot oil^1} 1000

Lemon oil²⁾ 2000

Lavandin oil³⁾ 400 Neroli oil 400 Petitgrain oil⁵ 100

Orange oil⁶⁾ 2000

Rosemary oil 100

8000

1) Comprises around 82 % of ingredients of list b); i.e. limonene, linalool and linalyl acetate

2) Comprises around 70 % of ingredients of list b); i.e. limonene, and terpineol 3) Comprises around 82 % of ingredients of list b); i.e. limonene, linalool, camphor, lynalyl acetate and terpineol

4) Comprises around 65 % of ingredients of list b); i.e. limonene, linalool, lynalyl acetate and terpineol

5) Comprises around 80 % of ingredients of list b); i.e. limonene, linalool, lynalyl acetate and terpineol

6) Comprises around 95 % of ingredients of list b); i.e. limonene and linalool 7) Comprises around 60 % of ingredients of list b); i.e. limonene, linalool, camphor and terpineol The addition of 4 to 10 parts by weight of 4-methyl-2-pentylpyridine (i.e. 0.05% to 0.15% of 4-methyl-2-pentylpyridine, percentage being relative to the total weight of ingredients of lists a) and b)) to the above-described composition enhances the naturality and the cooling effect, bringing a more zesty lime and sorbet aspect.

The perfuming composition of the citrus type was diluted in dipropylene glycol up to 10000 parts by weight; i.e 1990 to 1996 parts of dipropylene glycol was added respectively to the above-described composition comprising 4 to 10 parts by weight of 4- methyl-2-pentylpyridine.

Example 3

Preparation of a perfuming composition

A perfuming composition, of the aromatic type, was prepared by admixing the following ingredients: Parts by weight Ingredient

Citronellyle acetate 80

Isobornyl acetate 80

Linalyle acetate 1000

Artemisia oil^ 80

cedarwood oil 100

Cetalox^{® 2)} 20

Lemon oil³⁾ 400

Coumarine 160

Dihydromircenol 2000

Dipropylenene Glycol 800

Elemi oil⁴⁾ 100

Estragon oil⁵⁾ 40

Geranium oil⁶⁾ 40

Iso E Super^{® 7)} 800

Lavendin oil⁸⁾ 200

Linalool 800

Hedione^{® 9)} 800

Patchouli oil 400

Orange oil¹⁰⁾ 600

Amyle salicylate 200

Sage oil^U) 200

Terpineol 100

9000

1) Comprises around 36 % of limonene, and camphor

2) dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,l-b]furan; origin: Firmenich SA, Geneva, Switzerland

3) Comprises around 70 % of limonene, and terpineol

4) Comprises around 50 % of limonene and terpineol

5) Comprises around 4 % of ingredients of list b); i.e. limonene and eugenol

6) Comprises around 3 % of ingredients of list b); i.e. linalool 7) l-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)- 1-ethanone; origin: International Flavors & Fragrances, USA

8) Comprises around 82 % of ingredients of list b); i.e. limonene, linalool, camphor, lynalyl acetate and terpineol

9) Methyl dihydrojasmonate; origin: Firmenich SA, Geneva, Switzerland

10) Comprises around 95 % of ingredients of list b); i.e. limonene and linalool

11) Comprises around 23 % of ingredients of list b); i.e. camphor

12) Comprises around 82 % of ingredients of list b); i.e. limonene, linalool, camphor, lynalyl acetate and terpineol

13) Comprises around 65 % of ingredients of list b); i.e. limonene, linalool, lynalyl acetate and terpineol

14) Comprises around 80 % of ingredients of list b); i.e. limonene, linalool, lynalyl acetate and terpineol

15) Comprises around 95 % of ingredients of list b); i.e. limonene and linalool

16) Comprises around 60 % of ingredients of list b); i.e. limonene, linalool, camphor and terpineol

The addition of 2 to 4 parts by weight of 4-methyl-2-pentylpyridine (i.e. 0.03% to 0.1% of 4-methyl-2-pentylpyridine, percentage being relative to the total weight of ingredients of lists a) and b)) to the above-described composition enhances the cooling feeling and the freshness.

The perfuming composition of the aromatic type was diluted in dipropylene glycol up to 10000 parts by weight; i.e 996 to 998 parts of dipropylene glycol were added respectively to the above-described composition comprising 2 to 4 parts by weight of 4-methyl-2- pentylpyridine.

Example 4

Preparation of a perfuming composition

A perfuming composition, of the floral type, was prepared by admixing the following ingredients: Parts by weight Ingredient

Benzyl acetate 2000

Cinnamyl acetate 100

Phenylethyl acetate 100

Benzylic aclohol 200

Cinnamic alcohol 1400

Aldehyde cinnamic 40

Phenylacetic aldehyde 4

Benzyl benzoate 2000

Methyl benzoate 20

Dipropylenene Glycol 436

Eugenol 200

Indol 40

Methylisoeugenol 100

Phenethylol 1000

Triethynolamine 360

8000

The addition of 2 to 40 parts by weight of 4-methyl-2-pentylpyridine (i.e. 0.04% to 0.8% of 4-methyl-2-pentylpyridine, percentage being relative to the total weight of ingredients of lists a) and b)) to the above-described composition enhances the freshness and the naturality of hyacinth and lilac notes.

The perfuming composition of the floral type was diluted in dipropylene glycol up to 10000 parts by weight; i.e 1960 to 1998 parts of dipropylene glycol was added respectively to the above-described composition comprising 2 to 40 parts by weight of 4- methyl-2-pentylpyridine.

Example 5 Preparation of a softener comprising the invention's composition Table 1: Composition of the softener formulation

Stepantex VL90 A Diester Quat; Origin: Stepan

Proxel GXL; Origin: Arch The softener was prepared by weighting Methyl bis[ethyl (tallowate)]-2- hydroxyethyl ammonium methyl sulfate which was heated at 65°C. Then Water and 1,2- benzisothiazolin-3-one were placed in the reactor and were heated at 65°C under stirring. To the above mixture was added Methyl bis[ethyl (tallowate)]-2- hydroxyethyl ammonium methyl sulfate. The mixture was stirred 15 minuted and CaCl₂ was added. Then 0.5 to 1% by weight, relative to the total weight of the softener, of the invention's composition of example 3 was added. The mixture was stirred 15 minutes and was cooled down to room temperature under stirring (viscosity measure : result 35 +/- 5 mPas. (shear rate 106 sec- 1 ) ). Example 6

Preparation of a liquid detergent comprising the invention's composition

Table 2: Composition of the liquid detergent formulation

Concentration

Ingredients

[wt%]

Sodium C14-17 Alkyl Sec Sulfonate¹* 7

Fatty acids, CI 2- 18 and C18-unsaturated²⁾ 7.5

CI 2/ 14 fatty alcohol polyglycol ether with 7

17

mol E0³⁾ Triethanolamine 7.5

Propylene Glycol 11

Citric acid 6.5

Potassium Hydroxyde 9.5

Properase L⁴⁾ 0.2

Puradax EG L⁴⁾ 0.2

Purastar ST L⁴⁾ 0.2

Acrylates/Steareth-20 Methacrylate

6

structuring Crosspolymer⁵'

Deionized Water 27.4

1) Hostapur SAS 60; Origin: Clariant

2) Edenor K 12-18; Origin: Cognis

3) Genapol LA 070; Origin: Clariant

4) Origin: Genencor International

5) Aculyn 88; Origin: Dow Chemical

The liquid detergent was prepared by adding 0.5 to 1% by weight, relative to the total weight of the liquid detergent, of the invention's composition of example 3 into the unperfumed liquid detergent formulation of Table 2 under gentle shaking.

Example 7

Preparation of a transparent isotropic shampoo comprising the invention's composition Table 3: Composition of the transparent isotropic shampoo formulation

1) Ucare Polymer JR-400, Noveon

2) Schweizerhall

3) Glydant, Lonza

4) Texapon NSO IS, Cognis

5) Tego Betain F 50, Evonik

6) Amphotensid GB 2009, Zschimmer & Schwarz

7) Monomuls 90 L-12, Gruenau

8) Nipagin Monosodium, NIPA

The shampoo was prepared by dispersed in water Polyquaternium-10. The remaining ingredients of phase A were mixed separately by addition of one after the other while mixing well after each adjunction. This pre-mix was added to the Polyquaternium-10 dispersion and mixed for another 5 min. Then, the premixed phase B and the premixed Phase C were added (Monomuls 90L-12 was heated to melt in Texapon NSO IS) while agitating. Phase D and Phase E were added while agitating. PH was adjusted with citric acid solution till pH: 5.5 - 6.0 leading to an unperfumed shampoo formulae. The perfumed shampoo was prepared by adding 0.4 to 0.8% by weight, relative to the total weight of the shampoo, of the invention's composition of example 4 into the unperfumed shampoo formulation of Table 3 under gentle shaking. Example 8

Preparation of a eau de toilette comprising the invention's composition

The eau de toilette was prepared by adding 5 to 15% by weight, relative to the total weight of the eau de toilette, of the invention's composition of example 2 into ethanol under gentle shaking.

Example 9 Preparation of a soap bar comprising the invention's composition

The soap bar was prepared by adding under gentle shaking 0.8 to 1.5% by weight, relative to the total weight of the shower gel, of the invention's composition of example 1, 2, 3 or 4 into a melted and unperfumed soap bar formulation (Christal ST; trademark and origin : Stephenson Group limited) comprising water, Glycerin, Sodium Stearate, Sorbitol, Propylene Glycol and Sodium Laurate.

Example 10 Preparation of a structured shower gel comprising the invention's composition

Table 4: Composition of the shower gel formulation

Ingredients Concentration (wt

%)

WATER deionized 52.40

Tetrasodium EDTA ^1} 0.10

Sodium Benzoate 0.50

Propylene Glycol 2.00

Sodium C12-C15 Pareth Sulfate ²⁾ 35.00 Cocamidopropyl Betaine ⁾ 8.00

Polyquaternium-7⁴⁾ 0.20

Citric Acid (40%) 1.00

Sodium Chloride 0.80

1) EDETA B POWDER; trademark and origin: BASF

2) ZETESOL AO 328 U; trademark and origin: ZSCHIMMER & SCHWARZ

3) TEGO-BETAIN F 50; trademark and origin: GOLDSCHMIDT

4) MERQUAT 550; trademark and origin: LUBRIZOL

The shower gel was prepared by adding 0.5 to 1% by weight, relative to the total weight of the shower gel, of the invention's composition of example 1,2, 3 or 4 into the unperfumed shower gel formulation of Table 4 under gentle shaking. Example 11

Preparation of a transparent shower gel comprising the invention's composition

Table 5: Composition of the transparent shower gel formulation

1) EDETA B POWDER; trademark and origin: BASF

2) ZETESOL AO 328 U; trademark and origin: ZSCHIMMER & SCHWARZ

3) TEGO-BETAIN F 50; trademark and origin: GOLDSCHMIDT

4) MERQUAT 550; trademark and origin: LUBRIZOL The transparent shower gel was prepared by adding 0.5 to 1% by weight, relative to the total weight of the shower gel, of the invention's composition of example 1, 2, 3 or 4 into the unperfumed shower gel formulation of Table 5 under gentle shaking.

Example 12

Preparation of a milky shower gel comprising the invention's composition

Table 6: Composition of the milky shower gel formulation

1) EDETA B POWDER; trademark and origin: BASF

2) Texapon NSO IS; trademark and origin: COGNIS

3) MERQUAT 550; trademark and origin: LUBRIZOL

4) DEHYTON AB-30; trademark and origin: COGNIS

5) GLUCAMATE LT; trademark and origin: LUBRIZOL

6) EUPERLAN PK 3000 AM; trademark and origin: COGNIS

7) CREMOPHOR RH 40; trademark and origin: BASF The transparent shower gel was prepared by adding 0.5 to 1% by weight, relative to the total weight of the shower gel, of the invention's composition of example 1, 2, 3 or 4 into the unperfumed shower gel formulation of Table 6 under gentle shaking. Example 13

Preparation of a pearly shampoo comprising the invention's composition

Table 7: Composition of the pearly isotropic shampoo formulation

2) Jaguar C 14 S, Rhodia

3) Ucare Polymer JR-400, Noveon 4) Sulfetal LA B-E, Zschimmer & Schwarz

5) Zetesol LA, Zschimmer & Schwarz

6) Tego Betain F 50, Evonik

7) Xiameter MEM- 1691, Dow Corning

8) Lanette 16, BASF

9) Comperlan 100, Cognis

10) Cutina AGS, Cognis

11) Kathon CG, Rohm & Haas

12) D-Panthenol, Roche

The shampoo was prepared by dispersed in water and Tetrasodium EDTA, Guar Hydroxypropyltrimonium Chloride and Polyquaternium-10. NaOH 10% solution (Phase B) was added once Phase A was homogeneous. Then, the premixed Phase C was added, and mixture was heated to 75 °C. Phase D ingredients were added and mixed till homogeneous. The mixture was cooled down. At 45°C, Phase E ingredients were added while mixing. Final viscosity was adjusted with 25% NaCl solution and pH of 5.5-6 was adjusted with 10% NaOH solution.

The perfumed pearly shampoo was prepared by adding 0.4 to 0.8% by weight, relative to the total weight of the shampoo, of the invention's composition of example 4 into the unperfumed shampoo formulation of Table 7 under gentle shaking.

Claims

1. A perfuming composition comprising

a) 4-methyl-2-pentylpyridine; and

2. The perfuming composition according to claim 1; characterized in that the perfuming composition comprises 4-methyl-2-pentylpyridine in an amount comprised between 0.02% to 0.4% w/w, percentage being relative to the total weight of ingredients of lists a) and b).

3. The perfuming composition according to claim 1; characterized in that the perfuming composition comprises 4-methyl-2-pentylpyridine in an amount comprised between 0.4% to 1% w/w, percentage being relative to the total weight of ingredients of lists a) and b).

4. The perfuming composition according to any one of claims 1 to 3; characterized in that the perfuming composition further comprises a perfumery carrier.

5. The perfuming composition according to any one of claims 1 to 4; characterized in that the perfuming composition further comprises at least one perfuming co-ingredient.

6. The perfuming composition according to any one of claims 1 to 5; characterized in that the perfuming composition further comprises a perfumery adjuvant.

7. The perfuming composition according to any one of claims 1 to 6; characterized in that the ingredients of list a) and b) are present in the composition in an amount comprised between 5% and 90% w/w, percentage being relative to the total weight of the ingredients of the composition.

8. The perfuming composition according to any one of claims 1 to 7; characterized in that 4-methyl-2-pentylpyridine is present in an amount comprised between 0.01 % to 1% w/w, percentage being relative to the total weight of the perfuming composition.

9. The perfuming composition according to any one of claims 1 to 3, characterized in that the perfuming composition consists of

a) 4-methyl-2-pentylpyridine; and

b) at least one ingredient selected from the group consisting of at least one ingredient selected from the group consisting of eugenol, phenethylol, cinnamic alcool, benzyl acetate, methyl benzoate, cinnamyl acetate, phenylethyl acetate, phenylacetaldehyde, indol, bornyl acetate, isobornyl acetate, linalyl acetate, dihydromyrcenol, eucalyptol, linalol, terpineol, limonene, citral, camphor, menthol and mixture thereof;

10. Use as perfuming ingredient of a composition as defined in claims 1 to 9.

11. A method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of a composition as defined in claims 1 to 9.

12. A perfumed consumer product comprising a composition, as defined in any one of claims 1 to 9.

13. The perfumed consumer product according to claim 12, characterized in that the perfumery consumer product is a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin-care product, an air care product or a home care product.

14. The perfumed consumer product according to claim 13, characterized in that the perfumery consumer product is a fine perfume, a splash or eau de parfum, a cologne, a shave or after- shave lotion, a liquid or solid detergent, a fabric softener, a solid or liquid scent booster, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain-care product, a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a vanishing cream, a deodorant or antiperspirant, a hair remover, a tanning or sun product, a nail product, a skin cleansing, a makeup, a perfumed soap, a shower or bath mousse, an oil or a gel, or a foot/hand care products a hygiene product, an air freshener, a "ready to use" powdered air freshener, a mold remover, a furnisher care, a wipe, a dish detergent or hard- surface detergent, a leather care product or a car care product.